Bet
by Chaotic91
Summary: Dean/OLDER Claire. A simple bet landed Dean is quite a situation.
1. Chapter 1

I know, I know…

I have plenty of other stories to be working on, but this kept clouding my mind…

I am halfway through with my other stories, and this is just a one-shot for now.

Now, I am going to go back to my other stories.

I hope someone enjoys this…

I like how Older Claire and Dean are with each other, it is adorable.

~bye~

"You know Dean…" Claire stood next to her uncle's best friend, and the man she had known since she was ten. He was only 26, but became best friends with her father's twin years ago. Something about Castiel saving Dean and Sam, his little brother, from the streets…She never learned the full story, but she knew it was around the time her father was killed. He was currently washing dishes from dinner. Castiel had to work late so Dean promised to stop by and make sure 'the runt' had something to eat. "I am going to be 18 this week…"

"I bet that makes you think you are all grown up, huh?" Dean smiled toward her.

"More grown than you…" She shot back. Her favorite hobby was trying to irritate Dean Winchester, he was such a smug jerk, letting his looks get him out of everything… She always wondered how he could be so toned, but eat so much pie. It wasn't like he worked out a lot either, he was a car mechanic. Maybe it was more work than she thought? She shook herself from her thoughts when Dean walked to the fridge to pull out a beer, having finished the last of the dishes, and head into the living room. "Actually, I was hoping to get a present from you…" She was nervous, and a little disgusted, but Claire wasn't going to back down now.

Dean turned to her and let a classic smirk cover his face. "Oh? What do you want from me bratzilla? I already told you that I couldn't get you a car…" Dean warned. "Castiel has already threatened me in four different ways." The man sat down in the recliner and tipped his beer back, reaching for the remote.

Claire shook her head and twisted her hands nervously. "No, that wasn't it…" She swallowed, here goes nothing. "I wanted you to give me a kiss."

Dean choked on his beer, and ended up in a coughing fit for a full minute. "You want a what?" He asked as he stared at her in disbelief.

"I want you to kiss me." She said more surely. "You see, my friends have this disgusting bet going that they can get a kiss from you before graduation…" It wasn't a lie, her friends all thought Dean was the sexist man in town, and Sam too. "If I get a kiss first, they have to pay for my part of our trip to Mexico this summer."

"You made a bet to…" Dean rubbed his head, possibly to hide the discomfort he felt, or the headache. "No!" He said like it was the obvious answer. "Castiel would kill me, and brats aren't my type."

"Please! I can't afford that trip, and I really want to go…" She pleaded, even getting on her knees in front of him. "It only has to be a thirty second kiss, with tongue…"

"With ton- Nope." Dean stood up and headed back to the kitchen, and Claire followed. "Can't you ask Sam? He is closer to your age…"

"That wasn't the bet, and Sam is happily engaged." She reminded. "Trust me, this idea repulses me, but I really want that trip…" She reached for his bicep and squeezed gently, putting on her best 'Sam puppy eyes'.

"Nice try, but those barely works for Sammy anymore…" Dean countered.

Claire huffed and crossed her arms…"Come on! It isn't like it would be my first kiss, or are you that bad at kissing?" She taunted, hoping to hook him.

Oh, she did.

"Hey, I am a god in the kissing department, alright?"

"Prove it?" She challenged.

Dean looked down at her and sighed after a moment. "…Castiel doesn't find out about this?"

Claire grinned wide. "Nope."

"…Alright, but just one and I am going to be counting to thirty in my head because this is just plain creepy."

"You can count that high?" Claire faked surprise, and Dean shot her a look.

"Do you want this to happen?" He threatened.

"..Sorry, sorry, I will be good."

Dean sat his bottle down on the counter and turned to face the blonde. He paused and looked at her with confusion. "How will your friends know we did this, and didn't make it up?"

Claire pulled out her camera phone and smiled wide. "With proof."

"…I think the police call it evidence…" Dean groaned, his head was telling him how stupid this was but he shook it off. One kiss couldn't hurt anything. "Let's do this…I am going to have you swooning dorkerella"

Claire turned the recorder on, and sat it on the counter beside them then she stepped closer to him. "More like puking, Prince Onion breath..." When Dean only glared and didn't make the first move, she stood up on her toes and pressed her lips to his hesitantly.

Dean froze up for a moment, at how awkward he felt, but eventually relaxed against her. He slowly slide his hands around her waist and pulled her closer until their bodies touched. Her breast pressed against his chest, and she wrapped her arms around his neck.

Claire's heart was beating wildly, his lips were not as chapped and rough as she thought they were going to be. She pulled away, but only far enough to whisper "I thought you were supposed to be good at this, where is the swooning?"

"…Oh it is on now." He whispered back with a mischievous grin, his hesitation gone. Dean swallowed hard though, she had some soft lips and her body was so warm. He dipped his head back down to catch her lips, this time he opened his mouth and pulled at her bottom lip. When she gasped he took the opportunity to slide his tongue into her.

She moaned as tingles spread through her body, and her lower stomach ached. She could feel a strong pulsing between her legs when Dean forced her tongue to come play with his. His hands had started to wander up her body, groping her breasts before sliding back down to her rear. When he gently pulled her groin into his, she could tell he was hard and that made her knees weak. She pressed against him again and got a pleased growl from him.

All too soon the 30 second timer on Claire's phone went off.

Dean jumped and backed away, turning from her. "Well, there you go…" He coughed and knocked on the counter nervously, hoping she wouldn't walk around to see the bulged in his jeans. "I think that will be more than enough proof for your friends."

Claire was still working on evening out her breathing, and calming her lower body. "Yea-yeah, that should do it…" She stared at his back, his very well-muscled back. This was a new feeling for the Frog prince…

"Claire? Dean?" Castiel's voice broke through her lust filled thoughts. She straightened, and noticed Dean do the same.

"Yeah, we're in here Cas." Dean was the one to speak first.

Castiel walked in and raised and tilted his head at the two. "Is everything alright?" He could sense there was tension in the air.

"Yeah, fine Cas…" Claire put on her best fake smile. "I-I have some homework to do, so I am going to go to my room…" She kissed Cas on the cheek and gave Dean an awkward wave before bolting from the room.

"…Well, that was odd?" Castiel looked at Dean for an answer. "Are you two sure everything is okay? Did you two fight again?"

Dean turned and faced his best friend once his hormones stopped ragging. "Well, if she wasn't such a spoiled princess we wouldn't have to worry about that." Dean did his best to play it off, and Cas seemed to buy it.

"What am I going to do with the two of you?" Castiel sighed.

"Love us, feed us, and never leave us?" Dean batted his eyes and smiled. Cas only rolled his eyes. "Hey Cas, uh, I am going to get home…so I will see you later."

"Alright, thanks for checking on Claire tonight."

"Anytime…" Dean walked to the front door, but stopped to look down the hallway at the teen's door for a moment. He shook any thoughts he was having and laughed quietly.

"It must be a full moon or something…" Dean mumbled and walked out the door


	2. Chapter 2

This story probably isn't going to be very long, unless I can find someway to make it longer but I can't think of any good plot lines...So this will most likely only have one or two more chapters.

Enjoy

~Bye~

* * *

"What do you mean it doesn't count?" Claire said with disbelief at her friends. The three of them were walking home from school when she decided to show them the video.

"You can't ask him to kiss you!" Charlie scoffed. "That is cheating."

"How is that cheating, and no one mentioned anything about not asking before!?"

"We thought it was obvious..." Adam said with a roll of his eyes, he was dragged into this by their other friend, Alyssa. He bet on Charlie being the first to get Dean to kiss her, and if he was wrong he'd have to pay for the winners trip. "Of course Dean would give you a kiss if you asked him, he is a nice guy and has known you since we were brats..."

"Yeah, and the kiss has to be with actual feeling...Not pity." Charlie mumbled.

"Although, that video really looked liked you were getting into it by the end..." Adam added, and Charlie giggled.

"She looked like she was ready to jump up on the counter and spread her legs for him..."

"As if!" Claire laughed to cover up her blush. She really had enjoyed that kiss, Dean was a really great kisser.

Not that she'd ever admit that to him, or anyone else. Dean's ego was already too much to handle.

"No one is judging you..." At that moment the three happened to be walking by the auto shop Dean worked at, he was currently outside looking under the hood of an old car. "I mean...look at him." Charlie was practically drooling. It was a hot day, nearly 100 degrees and Dean was shirtless. His hands were black from oil; he reached up to rub the sweat off his brow, and smudged some across his head. His back was tan from hour in the sun, and you could see his muscles moving nicely under his skin as he struggled to remove a part from the car.

Claire felt her stomach tighten as she watched him, a pleasant ache thumping between her legs. She really wanted to deny he was attracted to him, but she'd have to be blind. What had that kiss awakened in her? Dean had always been the obnoxious 'older brother' type, he was a arrogant asshole on the best of days.

"...All I see is a smart mouth mechanic with a short fuse." She lied.

"Is that why you bought him that slice of pie in your backpack?" Adam mentioned, not believing her.

"Hey, sometimes the idiot gets so wrapped up in his work, he forgets to eat." She defended. "And Cas is too busy to bring him lunch today, so he asked me to bring him something after school."

"Sure." Adam smiled, still not buying it.

"Well, I see my free ticket to Mexico and a good time." Charlie grinned mischievously before jogging over to Dean. Claire and Adam looked at each other and shook their heads, sharing a smile.

"You know...for a computer nerd, she is pretty out going." Adam said, sounding a little jealous and following Claire over to the shop.

"Well, most computer nerds don't look like her..." She pointed out right before reaching Charlie again. She was smiling up at Dean, who had stopped his work the moment he saw her running towards him and smiled. When his eyes landed on Claire he gave the smirk he knew got under her skin and winked. In return she blew him a kiss before flipping him off; he just smiled wider and went back to listening to Charlie ramble on about her latest computer trick.

"That sounds...great?" Dean was so lost, computers were definitely Sam's area.

"My teacher thought so, I passed the class without even taking the final."

"Yes, we get it, you're a smart cookie..." Adam jumped in, nodding his head toward Dean. "What's up Dean, isn't this that crp car you've had in your drive way forever?" He looked at the car, and Claire smiled at the way Dean's eyes lit up.

"Isn't she beautiful? I finally got enough money saved to fix up my old man's impala." Dean pointed at the car excitedly.

"Please don't get him started..." Claire groaned.

"Shut your pie-hole." Dean glared.

"Speaking of pie..." She reached into her bag and pulled out the container. "I guess you don't want this then?" Dean grinned like a five year old with candy, and reached for the box but Claire pulled it away. "What do you say?"

"...Claire Novak is better than Dean Winchester in every way..." He sighed out, like he'd done this a hundred times.

"And...?" Claire waited.

Dean seemed to have had enough, and crossed his arms. "...And Dean Winchester can tell Castiel Novak the real reason he got a free paint job on one side of his car."

"Touchy, touchy...here." She gave in, handing the pie over. "Wash your hands before you open it though..."

"Don't tell me what to do..." Dean said, and Claire just rolled her eyes.

"Hey guys..." The three looked at Adam. "I have to get going, practice starts soon."

"Alright, call me tonight so we can study our finals!" Claire called after him, while he walked away.

"Yeah, pass your finals and be...you know, a geek like Sam. With that lawyer Degree on the way." Dean yelled after him. Adam laughed and gave a thumbs up. Dean had only discovered Adam was his half brother a few years back, but he didn't have any trouble accepting him. He had a really big heart for family. Okay, so mybe he wasn't always an ass.

"Oh crap...!" Charlie slapped her hand over her forehead. "I left your notes for the history final in my locker!"

"What? How could you do that, I asked you if you had them!" Claire sounded panicked. "I need those!"

"Sorry, I was just distracted by my project that I forgot to grab my binder! Dean, could you give me a lift back to the school?" Charlie looked up at him pitifully, but winked at her when he nodded his head and turned away. "I guess I can close up a little early today."

Claire suddenly understood what was happening. Charlie forgot the notes on purpose, and she was trying to get some alone time with Dean.

So it was game time. Well, she was ready to play.

"Oh, Charlie just let me go. I mean, you live right up the street and Dean can just take me to his place until Cas gets off." Charlie glared at her.

"No, I insist, I was the one that forgot them after all."

"Actually, Claire's way makes a little more sense Char." Dean said, pulling his shirt over his head and hiding this gorgeous abs. He picked up his pie. "I am sure Claire doesn't mind going for you, since they are her notes anyway?"

"Of course not." She agreed then gave Charlie a smug, 'I win' smile.

"...I can't argue with the driver." She smiled and then mouthed to Claire, once Dean turned around, that this wasn't over. "So...I'll see you guys tomorrow?" Charlie turned to walk away, stomping her foot along the way.

She turned toward Dean's running car, a little too pleased with herself and oddly relieved.

* * *

Claire sat quietly in the passenger seat, her notes now safely in her backpack; she was lost in thought, how was she supposed to get Dean to kiss her again? She glanced at him, he was nodding his head to the music and seemed to not pay her any mind. This wasn't the first time she'd went home with Dean, he had babysitted her a lot growing up and it was some of the best memories she had.

"If you keep staring I am going to start charging you." Dean's voice snapped her back to the present, she didn't realize she'd zoned out with her eyes still glued to his face. She was about to tell him he'd make a great circus attraction but stopped herself. If she was going to get that kiss, she'd better turn on some charm.

"I'd pay it, if it meant I could see you." She hoped he actually bought that, but his suspicious glare said otherwise.

"...Are you hitting on me?" He asked, pulling into his driveway.

"After that kiss we shared, I couldn't help but notice a few things about you..." Claire tried again. It wasn't that far from the truth, that kiss did make her notice Dean in a different light; like how his eyes were the most beautiful green she'd ever seen, or the way his lips twitched before he was getting ready to say something sarcastic or funny.

"I think you've been studying too hard." Dean climbed out of his car, Claire not too far behind him, and unlocked his front door; he wasn't sure what was going on, but it didn't sit right in his gut. If he was going to be honest, he'd felt something when they kissed but he was going to do the sane thing, and not mention it until it faded away.

"Oh come on Dean, you felt it too right?" Claire followed him into the one bedroom home, it was small but big enough for him.

"Claire, listen..." He faced her. "It doesn't matter what was felt, it isn't-" Dean stopped what was going on hit him. He crossed his arms and gave his best glare. "This is about that bet isn't it?"

"What?" She did her best to act surprised. "Dean, I just realized how attractive, yeah okay..." Claire sighed in defeat, realizing how ridiculous she sounded. "Apparently you have to give me a kiss on your own free will...I can't ask for it."

"This is getting to be stupid..." Dean huffed out an unamused laugh, walking to his fridge to grab a beer. "Well, more stupid."

"Pleeeease?" She stepped closer to him, a sweet smile on her face, and grabbed his arm like before. He was so warm and smelled like sweat and oil, which turned her on for some reason. She'd always went for the preppy boys, but Dean was pretty much the opposite of that in every way so it was confusing. She let her thumb rub gently on his dirty skin. "My birthday is tomorrow, it isn't like this is really illegal. Just one more kiss and we can forget any of this ever happened, but you have to want it."

"Fine."

Claire felt her heart jump, she wasn't expecting it to be that easy.

"Really?"

Dean nodded, taking another drink of his beer. He stepped back from her grip, realizing it was making his chest feel odd, and walked around her. "But we are going to do this my way."

There is was, Claire sighed, the catch. "Where are you going?" She asked as Dean pulled his key out of his pocket and headed for the shower.

"It's where are we going." When Claire gave him a confused look, he grinned his signature grin.

"I am going to take a shower, and then we are going on a date, your royal pushiness. If I am going to have to be your boy toy, you're going to have to buy me dinner first."

"But I already bought you pie!?" She yelled after him, but he had already disappeared. "Sam is right, you are a jerk." She laughed to herself, trying to push down the excited feeling in her stomach.


	3. Chapter 3

Next chapter is the last chapter, I probably could have squeezed it all into this chapter but I have a thing about even numbers...

Shouldn't take me long to get it finished.

Enjoy

* * *

Claire watched Dean shovel food into his mouth and scoffed. "And women find you attractive?" The two were currently sitting in a booth at a small diner up the road from Dean's house. He gave the girl a smile, mouth still filled with food. She shook her head at took a sip of her soda to hide her own smile.

"I'll have you know, women love me." Dean added after swallowing. "But it is you that is supposed to be making me swoon, remember?"

"How could I forget, you keep reminding me." She had to make Dean want to kiss her, of his own free will. So the two had been 'hanging out' a lot more in the last few days. That first night, Dean actually made her buy him food and then do his laundry! The second day was her 18th Birthday, she went shopping with Castiel that morning and had lunch with him. Instead of going out with her friends, or enjoying her birthday gifts, the rest of the evening was spent helping Dean fix up that damn car of his in the shop, but he actually spoke with her while he worked and that made the time fly by. It was so easy to talk to Dean about nearly anything. She even learned a few of Dean's favorite things, like classic music made his eyes light up the same way talking about his car did. He also bought her a beautiful bracelet, he said the odd markings engraved on it was a symbol for protection. Claire rubbed the gift on her wrist with a smile and glanced over to see him taking a large drink of his soda. She had to admit, Dean always cleaned up nice. He was wearing a stainless blue T-shirt and dark blue jeans. Claire had never seen him in anything but oily work clothes or pajamas, when he stayed the night at her home because Castiel insisted he had too many beers to drive. His hair was short, but you could tell he combed it. She suddenly felt like her white tank top and worn out blue jeans were not enough.

"So, what's with the hair?" Dean brought her out of her thoughts and she touched the braid on one side of her head that lead up to her scalp. She shrugged.

"My friend wants to be a hairstylist, so I let her experiment with my hair." She said nervously. "...Do you not like it?"

Dean smiled and shook his head. "It's nice, different but nice." He leaned forward some, reaching out to gently run a hand over her head and down her braid. He held the end of it and rubbed it between his fingers. "More importantly, do you like it?"

Claire felt butterflies at the touches and looked away from those green eyes to regain some focus. She nodded. "She was going to do more, but I told her I liked it like this..."

Dean played with the tip of her braid for a bit longer then let another grin cover his face, he gave her hair a slight tug then let it fall and leaned back in his seat. "I'm glad to hear that, I thought you were going to be one of those girls when you were younger."

Claire knitted her eyebrows together in confusion. "Those girls?"

"Yeah, you know, the ones that only want to 'fit in'." He took another bite of his burger before continuing. "The brainless air-heads that walk around desperate for approval."

"Oh, you mean like the girls you date?" Claire threw back. Dean did have a reputation of dating the stupidest girls. Claire could still remember the last one he brought by. She was only a pole away from stripper status.

"Well...I wouldn't call it dating." Dean said with a slight laugh then cleared his throat. He forgot who he was talking to. Claire waited for him to clarify. "Well, I..." He sighed. "It was more of an...understanding?" He hinted. Claire stared for a second then scoffed in disgust when it clicked.

"You brought your flings over to my house? Gross."

"Hey, that was years ago alright...I'd like to think I've gotten better." Dean defended. "I was a bad kid, with a lot of problems and I took it out on the world around me."

Claire did admit it was a few years back when that happened. In fact, she couldn't recall the last time she saw Dean with anyone. "Well, I was one of those girls...for a while." She cringed at the memories of her old self. "...But something happened that made me change, I finally saw what I was around junior year." She really didn't want to talk about that right now, so she quickly added "What made you change?"

Dean could sense a story there, but also knew the signs to leave a subject alone. Maybe he'd find out later. "My brother, Castiel...your dad." He said the last part gently. He hadn't tried to talk about James in a long while.

"My dad?" Claire was surprised, she knew her father was killed and it involved a situation with Dean, Sam, and her uncle but she was too young to know all the details back when it happened. "How?"

"Yeah...hey, maybe you should ask Cas about this story?" Dean didn't want to get in the way, or say something he shouldn't about this subject. "Just know that your dad saved my life." He smiled at her sadly, the memories of that day floating to the top of his mind. Gunshots echoed through his mind along with screams. "He was a great guy."

"Yeah, I wish I could remember more about him." Claire admitted, she had only been seven when he died.

"You got Cas though." Dean added to cheer her up, seeing Claire's face fall slightly at the subject. He didn't like to see her sad. She did give a smile at that.

"Yeah, I don't know what I'd do without him."

"Starve." Dean nodded. "I would starve." Claire couldn't help a laugh that escaped at how seriously that was said. Dean had been known to get so lost in his work that he'd forget to sleep or eat. She could remember him outside her house once, at around three in the morning, trying to get Castiel's old car working. Cas had to nearly wrestle him inside to sleep, he also did things like that when he wanted to escape his feelings. Claire opened her eyes slightly in surprise, she didn't know she knew so much about Dean. He'd always just...been around. Until these last few days, she hadn't realized how much his presence was just expected.

"So..." She needed to get talking before she got lost too deep inside her head. "Do you have a girlfriend now?"

He was the one to laugh at that, finishing off his burger. "If I did, I wouldn't be doing this bet of yours." She was a little too relieved to hear that as she leaned back to let the waitress take their plates.

"You didn't even eat?" Dean frowned when the waitress left to bring back a slice of pie as requested.

"I'm not very hungry." She continued before he could argue. "Have you not found the right person, or...?"

Dean smiled in thanks to the waitress when she sat his pie and the check down before looking back at Claire. "I just haven't been lookin' I guess. I feel like I got too many issues to drag someone into, you know?"

"You're not that bad Dean." She kicked his leg gently with her foot. "Sure, you can be moody sometimes and your mouth never takes a break-"

"Is this you trying to impress me? 'Cause I'm not feelin' it." Dean interrupted, taking a large bite of pie.

" **but**..." She gave him a glare for cutting her off. "You have a big heart, more than you'll admit, and you care about other people not just yourself. Come to think of it, you've always been there if Castiel or I ever needed you." There eyes met when she spoke the last sentence, but she lost her nerve to keep the contact when he let a sexy smile appear slowly on his face. "For what it's worth, I think you're a pretty great guy." She didn't have the guts to look him in the face yet, just in-case he had that obnoxiously adorable but totally smug smirk. This was ridiculous, when did she become shy?

Claire looked like she was concentrating a little too hard on the table, and Dean couldn't stop from smiling; it wasn't his normal 'I think I am adorable, and you should too' smile, but a real one. The things she had just said made him feel fluttery on the inside. He shrugged it off, so he couldn't describe it but it felt nice but also terrified him. "Well, here I thought you just saw me as an annoyance all these years." He decided to break the silence the best he could. She looked up at him and smiled gratefully.

"Oh, you were that too, so much that." She joked along. "Seriously, I think you get stuck on 'asshole' mode way too often."

He rolled his eyes and relaxed a bit more, comfortable with their normal rhythm. "Only because you like to be a royal pain, princess." He winked at her while he pulled out his wallet. Claire gave him a confused look.

"I'm not paying this time?"

"I eat too much for you to be buying all my meals." He threw a tip on the table then stood to head the register. "Besides, don't you need to save up for that trip? You can bring me a souvenir."

"If I ever get to go..." She muttered out, following him. Why was it so hard to get a kiss from this man? Her trip was looking more and more distant. Maybe she should just suck it up and ask Castiel for the money, but her uncle already over works himself just to save up for her college and expenses; asking for more, just seemed wrong. She had tried to get a job at the grocery store, but it never happened. No place wanted to hire an inexperienced worker now a days.

"Hey!" Claire snapped out of her thoughts at Dean's voice. He was by the exit and giving her a questioning look. "Are you coming, or are you just going to stand there all night?" She glared but followed after him. The warm air outside was a refreshing feeling after being inside the air-conditioned building. She was going to walk to the car when Dean headed the other way.

"Where are you going now?" She sighed out, but followed.

"I thought it would be a great night for a walk around the block." He shrugged like it was nothing. Claire jogged to catch up to him.

"Do you normally go for random strolls at night?" Claire bumped against him playfully. "You could get kidnapped and used to make pies by a deranged couple.

"Okay, first off, you've been watching too many horror movies..." Dean pushed back, making her stumble slightly but laugh when he continued. "Secondly, I can think of worse things than becoming pie. I used to walk around at night all the time, easier not to be seen by the cops that way."

"Oh, such a bad-ass." Claire looped her arm around his without thinking too much about it, but she didn't miss Dean smile at her. "Castiel would freak out if I wasn't in by six." Claire could already see his worried face when she came home an hour or so late a few times. She got an earful those nights.

Dean shrugged again. "Hey, at least you had someone there to freak out. My old man was in and out of our lives so much, he never felt much like a parent."

"What about your mom?" Claire asked innocently, She had heard a few stories about their father, she had never heard anything about the Winchester boys's mother. Dean paused to look inside the window of a closed store, or to just hide his face for a moment.

"Ah, well, mom died when I was six...So I don't really remember much about her." Claire tightened her hold on his arm until he looked at her.

"I'm sorry, I know how that feels." He gave her another smile, but his eyes looked sad. He seemed to shake it off after a moment and continued to walk.

"Hey...isn't that Charlie?" Claire followed Dean's gaze to a group of teens standing at the corner laughing. It was a few of her friends from school, including Charlie.

"Sure is, looks like they just got out of a movie." She smiled when the red head looked over at the two and waved them over, recognizing the two quickly. "These are the kids you can thank for making that bet you love so much."

Dean looked at the group as they got closer. "Well, that explains why I was getting hit on more often..." He recognized a couple of the girls who had randomly stopped by at the shop to ask him for car advice. He had to admit, if it wasn't for their ages, and the fact he was trying to be a better person, he might have took the bait. "Teenagers are weird..."

"Yep, come on, let's get this over with." Claire knew what was going to happen, Dean was about to get a huge ego boost from these girls as they attempted to gain his affections; and for some reason that made her grumpy. She squeezed his arm tighter before letting go to walk over to her friends. She was surprised to feel Dean grip her wrist and pull her back into him. "What are you doing?" She looked up at him, confusion clear on her face.

"I'm not walking into that, so I am doing exactly what you said and get this over with." He was having fun these last few days, but enough was enough. Dean leaned down to capture her lips before she could respond. He let go of her wrist to tilt grab her jaw and tilt her head back more. It didn't take long for Claire to respond, wrapping her arms around his neck and pulling him closer. She opened her mouth, giving him permission that he took without thought. Their tongues clashed for dominance, but Dean eventually won, his hands finding their way around her hips to pull her as close as possible with clothes on. Claire felt her knees shake as he greedily explored her, and she dug her fingers into his shoulders to keep from falling.

Dean let go when air became a problem, and gasped. Claire did the same, but her eyes remained shut and her cheeks were tinted a light pink. When she finally opened them to look up at him, her eyes met his. She bit back a groan at the intense stare he was giving her and dug her nails back into his shoulders; pulling him down. She wanted to kiss him more, longer and with less clothes. Dean seemed to agree by the way his eyes closed slightly and he licked his lips. She felt his hands on her hips, like Dean was about to yank her against him.

"Whoa..." Charlie's voice brought the two back to reality, and Dean pulled away. They were in the middle of a sidewalk, with a group of teens watching them basically make out. Claire reluctantly let her hands fall away and bit at her lip to try and calm her body. She looked up at Dean once more, who looked like he was concentrating on something really hard. Her eyes traveled down his body and another pulse of pleasure shot through her stomach at him trying to hide his erection with his T-shirt.

"I'm..." Dean coughed. "I'm going to go get the car warmed up...Don't take too long." He turned way quickly and stumbled off, giving a wave over his shoulder when Char said goodbye.

"Oh...my god!" Charlie and the rest of the group ran over to her. "That was the hottest thing I've seen in months!" One girl squealed. "How did it feel?" Before Claire could answer her other friend jumped in. "It felt amazing, anyone can tell that by the look on her face."

"Okay guys, I think it is official, forced or not forced, that was so hot you win the bet Claire." Charlie frowned, but smiled quickly after. "You get to go to Mexico for free!"

"O-oh, yeah, great." Claire was still trying to get her thoughts from making out with the gutter. So that was why Dean kissed her, no one could deny what was right in front of them. So that meant it was over, she could go back to her normal ways and Dean would just be Dean again.

"You okay Claire?" Charlie asked, sounding concerned. "For a second there, you kind of looked like you were going to cry."

"I'm fine, everything is fine." She pulled away from the group. "I got to go, I'll see you guys later!" She called over her shoulder to a confused Charlie as she jogged back to the vehicle.

Dean rubbed his head, he was sitting in the driver seat, and let out a sigh. He did the right thing, putting an end to this stupid bet, but he felt bad about it to be honest. "I shouldn't have even played along t begin with..." He said to himself. It was cute in the beginning but tonight he felt a shift in the relationship he had with Claire, before all this she was just his best friend's niece but looking at her now; Claire wasn't a little girl anymore, and tonight made him think she was actually interested in him. She wasn't though, Dean let his head fall back on the seat. It was all for a bet. He straightened when Claire pulled the passenger door open and climbed in. "I should get you home before Cas gets there to lecture me abou-mhn!" Dean was not expecting the blonde to climb over and kiss him. He kissed back for a moment, when his brain caught up, then pulled away. "What the hell, was that kiss out there really not enough to convince them!?" He pushed her back over to her side. "What do they want, a fucking step by step?"

"That wasn't for them." Claire stated, leaning forward to kiss him again but he stopped her with a hand on her stomach.

"Then why are you? What are you after now?" He didn't mean for it to sound so defensive, but he was being thrown off his feet here and Dean didn't like being in the dark; you get hurt that way.

"Dean...I just...I want to make a new bet." Claire said, putting her hand over the larger one against her stomach.

"Forget it, I am done with this whole-"

"I bet I can make you fall for me, like I am for you." She forced the confession out, hoping it didn't blow up in her face. Dean seemed to freeze up for a moment, so she took the opportunity to lean forward and whisper in his ear. "Let me stay the night with you?" She felt his grip tighten for a moment, and his jaw clenched. She smiled when he finally released her to grab the wheel and turn toward his house, his mind apparently made up.


	4. Chapter 4

This starts out with the sexy parts.

There will be a sequel to this in the future, if anyone is interested in reading it.

Enjoy

* * *

The door to Dean's home burst open and he stumbled in with a laughing Claire, who currently had her legs wrapped around his waist. Their mouths came together in a quick passionate kiss before he pulled away carry the blonde safely to his room. Claire wasn't making it easy on him either by biting, sucking, and kissing his neck the whole way. She let out another laugh when he tossed her on his bed with a low growl. He pulled his shirt off and watched in appreciation as Claire did the same. Fuck, she wasn't wearing a bra. Her breast bounced gently as the tank top was removed, her nipples looked perfect and already hardening. Dean swallowed and held back a groan as his cock jumped at the sight, making his already tight pants that much more uncomfortable. The teen crawled over to him , standing on her knees at the edge of the bed. She kissed down his well toned stomach slowly as she unbuttoned his jeans.

She was so turned on that she was shaking, and Dean's calloused hands running through her hair and roughly down her back made her gasp. His hands dipped into her pants, gripping her ass before sliding back up to her head. Claire kissed and sucked him through his boxers, he groaned letting his head hang back for a moment. Finally she pulled down the black material and watched him spring free. She could see why he was so smug now. Dean was definitely the biggest she'd ever seen. She licked the tip, then kissed, listened to him suck in a sharp breath of air before taking him in her mouth slowly. Dean's hands immediately tightened on her head, but he didn't force his way deeper. He didn't want to hurt her, but god she was driving his nuts already and she was only at the tip. It wasn't too long before she had him at her throat, slowly trying to get passed her gag reflex. Her head was bobbing at a steady pace in no time, Dean sliding inside of her with little problem.

"You're...you're killing me." He whined out, her hands firmly on his hips to remind him to control himself. She would've smiled if she wasn't busy. He nearly sounded like he was begging. How long had it been since Dean had sex? She didn't get to think on that too long because the light brunette had found a way to keep himself preoccupied. He had slid her pants down to her thighs and reached into her panties. Claire nearly choked when his fingers teased her, one ever pressing inside her. "You're already so wet." He huffed out in a pleasured tone, Claire couldn't see his face at this angle but she'd bet money he had that smirk again. "That excited by me, huh?" She needed to remind him that she wasn't the only one. So she gripped his hips tighter and sucked him hard, nearly taking all of the erection.

"Sh-shit!" He growled, moving his hips roughly for a moment before regaining some control. Claire closed her eyes tight, but didn't try to stop him. She felt his hand pull away from her and the other grip the back of her head, pulling her free of him. His kiss was rough and demanding as he fell back onto the bed with her. The rest of Claire's clothes were quickly done away with as he climbed on top of her. She locked her legs around his waist, sighing at the feeling of skin on skin. The two made out passionately for a few minutes, while Dean slid a hand between them to prepare her.

"Enough..." Claire moaned out, stopping the two fingers he had moving inside her. "It's enough, I want you." That was more than enough for Dean as he quickly removed his hands and lined himself at her entrance. The first push inside made her wince and bite back a painful yelp. Dean caught on though.

"You're not a virgin, right?" He huffed out, suddenly worried he was going too fast. Claire shook her head.

"N-no, It's just been awhile." She answered, leaving out the 'and you're huge' part. Dean's head was big enough, she smiled at him. "I'm fine, really, don't stop." He gave her a look, but pressed deeper with a groan. She was fucking tight. After a tense minute or so, he was buried within her to the hilt. He kissed her neck and jaw gently, seeing the pained expression she wore. He was trying his best to be still, but Claire didn't seem to want that; her hips rocked into him, and she clenched around him. "Move." She whined, and Dean's control snapped. His pace was slow and constant at first, but it quickened steadily until his headboard was hitting the wall with each thrust.

"Oh...God..." He growled, his head buried into Claire's neck; her fingers racked down his back, leaving scratches that would last for days. Her legs clung to him desperately as she tried to meet his thrusts, the pain she had felt in the beginning giving away completely to pleasure. She threw her head back when he hit that special spot inside her and moaned his name.

"Ah...Dean...I...I'm...aah! There! More!" He had hit her sweet spot, and she arched her back; her body tightening around him.

Dean's fingers dug into his mattress as his pace became more chaotic, he was close and so was she. Claire gripped his head, pulling him into a rough kiss as she came, her scream swallowed by his lips. With a few more pumps he followed her over the edge, collapsing on her. Her legs shook, and where heavy as lead, but she managed to wrap them back around that beautiful body and hugged him closer as she came down from the bliss.

"...Awesome..."Dean spoke lowly, voice filled with sex. He slide down her body slightly, pulling out of her in the process, to rest his head on her bare chest. She smiled lazily, playing with his sweaty hair while he kissed her breast leisurely.

"Very awesome..." She giggled, loving the weight of him on top of her. She felt completely safe when his arms wrapped around her.

"Oh, shit!" His head snapped up to her in sudden fear. "I didn't use a condom!" She kissed his forehead to try and calm him, still to high on good sex to be so frantic.

"Relax, you baby, I am on the pill." He did relax a little at that, but still seemed worried. It faded quickly enough when she leaned forward again to kiss his lips. He smiled as she pulled back and laid his head back on her chest.

There was a lot to talk about, and more than a few complications caused by their decision, but for the next few hours, they were the happiest people on the planet.

* * *

"So, you're not going to fall for a hunky, accented beef head while you're there...right?" Dean grinned, leaning against his truck. The two were at the airport, Claire getting ready to leave for her trip. Castiel had said his goodbyes to her before work that morning and Dean had promised to get her safely on the plane.

"Why would I do that, when I have a perfectly good, 'Hunky Beef-head' right here?" She grinned back, stepping closer to the man she was falling hard for. He pulled her against him with a hand on her hip.

"Just keep that in mind while you're sneaking those margaritas." He whispered, kissing her fully. THe two hadn't told anyone they were together, it was still new after all, but it was unlikely they would run into anyone they knew here; considering her friends had already went inside the airport. She opened her mouth to let his tongue dominate her, wrapping her arms around his neck. She pulled back and giggled.

"Jealousy looks good on you Dean. Green is definitely your color..." She said while looking into those gorgeous green eyes. "Definitely. I'll be back before you know it..." She reassured him, pecking his lips one more time before pulling away to pick up her bag. "Will you wait for me?" She said it jokingly, but had to stop herself from jumping into the man's arms at the genuine look he gave when he responded.

"You bet."

Their future was unsure, but Claire wanted to be apart of this man's life as more than 'His best friend's niece'. She wanted to be someone special to him, and she would do everything she could to make him feel the same way even if it meant facing her Uncle and the rest of the world.


End file.
